In early 2010, A.V. Club writer Nathan Rabin decided to listen to and write about the bestselling, zeitgeist-friendly CD series NOW That’s What I Call Music! in chronological order. Each one of the 37 American NOW! collections compiles a cross-section of recent hits from across the musical spectrum. Beginning with the first entry from 1998, this column will examine what the series says about the evolution and de-evolution of pop music.

All pop music lovers eventually become their parents. They reach a tipping point, sometimes but not always in their early to mid-30s, when the slang, music, beats, and obsessions of youth culture stop feeling fun and exhilarating and become strange, foreign, and at least mildly disconcerting.

I experienced that profound disconnect with what the young people are listening to these days when I first heard Soulja Boy Tell Em’s “Crank That (Soulja Boy)” for the first time. It wasn’t just that I couldn’t relate emotionally to its lyrics like I do with, say, Kanye West or Little Brother. I honestly had no fucking idea what Soulja Boy was saying. It was as if he was speaking in a different language because, in a sense, he was: “Crank That (Soulja Boy)” delves so deep into obscure Southern hip-hop slang that it bears only a passing resemblance to the Queen’s English. Once upon a time I kept abreast of hip-hop slang, but I couldn’t have been more confused by “Crank That (Soulja Boy)” if it had been written and recorded in backwards Esperanto.

In a deliciously redundant gesture, Soulja Boy Tell Em includes his name in both his signature hit and in his album title—Souljaboytellem.com—which helpfully also doubles as his website URL. Never one to leave well enough alone, Soulja Boy begins the song by once again announcing his name. If nothing else, Soulja Boy’s compulsive need to recite his name in ways that would embarrass Mike Jones (Mike Jones! Mike Jones!) makes it highly unlikely listeners would ever find themselves thinking, “I really like that ‘Crank That’ song. I wonder who recorded it?”

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After getting that important piece of business out of the way, Soulja Boy then begins shouting about supermanning hos and cranking that Robocop in a hoarse rasp so mumbly and incomprehensible—trust me, I know from mumbly and incomprehensible—that it sounds as if he recorded the song with a mouth full of Jolly Ranchers. Being white and old, I had no idea what those phrases meant so I had to resort to the invaluable, often unreliable online cheat sheet that is urbandictionary.com. (Still can’t figure out what the “Robocop” part means, though.)

If “Crank That (Soulja Boy)” sounds like something a stoned teenager might record via a cheap computer program, that’s because it is. It was recorded using a program called FL Studio and sounds like it: “Crank That (Soulja Boy)” repeats a few core elements over and over and over and over again until it’s bludgeoned listeners into submission to the point where they’ll do a stupid dance or engage in an unsavory sex act just so Soulja Boy will stop shouting about Supermanning hos and compulsively repeating his name. “Crank That (Soulja Boy)” is ugly in its brutal simplicity, a chant-along work of almost hypnotic idiocy.

Of course, Soulja Boy Tell ’Em didn’t make the song for middle-aged white critics; he made it for clubs and barbecues and cars with booming systems. I started this project at least partially out of a regressive sense of nostalgia for the disposable pop schlock I listened to at the end of college; at this point I’m confronting fairly recent pop music whose appeal and meaning sometimes eludes me. Then again, I don’t want to turn into one of those shrill sorts who condemn what they don’t understand. That said, “Crank That (Soulja Boy)” is complete horseshit. Incidentally, the music video for “Crank That (Soulja Boy)” has been viewed over 93 million times on YouTube. Ninety. Three. Million. Times. I will leave it up to you to decide whether that’s a sign of an impending artistic apocalypse or merely a tribute to the commercial appeal of a cute kid with a catchy song and infectious dance.

Kanye West is a controversial figure around these here parts. People who know him only via his television-specific Tourette’s, constant public temper tantrums, and hit singles tend to dismiss him as an arrogant superstar. But that’s incredibly reductive, because Kanye West is ultimately everything. He’s self-deprecating and obnoxiously self-aggrandizing. He’s pop and underground, a dandified metrosexual and a paparazzi-abuser with an amusingly unconvincing thug swagger. He’s a man torn forever between his insatiable appetite for sin and his hunger for salvation and redemption, “Drunk And Hot Girls”” and “Jesus Walks.” His entire public career sometimes looks like an open-ended piece of performance art whose meaning remains unknown even to Kanye himself. I am Kanye. You are Kanye. Kanye is everyone and everything.

Like so many of Kanye’s songs, it’s primarily concerned with the gift and the curse of super-celebrity. “I had a dream I could buy my way to heaven / When I awoke I spent that on a necklace” West laments in the first line, establishing a tone that alternates between frank, brutal self-reflection and spacey self-mythologizing. Kanye’s tormented by his insatiable desire for money, clothes, women, status, and power, yet he never stops striving for transcendence and salvation.

“Can’t Tell Me Nothing” oscillates between flagrant abuse of the English language—West drops a syllable from “apologizing” so that it will just barely rhyme with “collagen”—and rhymes so cheesily clever that no less than Lil Wayne borrowed them (with full credit, surprisingly enough) on Tha Carter III. “Can’t Tell Me Nothing” is messy, funny, borderline profound, and sometimes mannered and stiff. In other words, it’s Kanye in a nutshell.

“Can’t Tell Me Nothing” contains some clumsy and flat-out stupid lines, but nothing can compete with “I’m about to strip and I’m well equipped/Can you handle me the way I are” and “Baby if you strip/you can get a tip/’cause I like you just the way you are,” the alternating boy/girl choruses of Timbaland and Keri Hilson’s “The Way I Are.” (And we wonder why little Jimmy is falling behind the rest of the world when it comes to using the proper tense.) But “The Way I Are” boasts such a slinky, irresistible electro-funk beat that the words are largely irrelevant. It’s entirely possible to write a perfect R&B song with idiotic lyrics. Case in point: Keri Hilson’s current single, “Pretty Girl Rock.” I love words, yet I nevertheless fell deeply in love with a song with lines like, “My name is Keri, I’m so very / fly oh my it’s a little bit scary / Boys wanna marry / Looking at my derri / ere, You can stare but if you touch it I’ma bury.” Just as defense trumps offense in football, incredible production almost invariably trumps lyrics in contemporary R&B.

Pretty-girl-rocker Hilson is certainly easy on the eyes, but is she a sentient suicide risk? That’s the bold assertion of Sean Kingston, a husky teen from Jamaica whose breakthrough hit generated controversy for its line, “They only wanna do your dirt / They’ll have you suicidal, suicidal / when they say it’s over.” Apparently pop radio found the “suicide” line in questionable taste, but when you’re a teenager with a body full of hormones and a mind full of drama, getting dumped by a beautiful girl really is a matter of life and death. “Beautiful Girls” owes much of its popularity to a crowd-pleasing sample of Ben E. King’s “Stand By Me,” though the plus-sized performer missed a golden opportunity for an obscure inside joke by not making a video in which Kingston and three of his friends discover a dead body and learn all manner of life lessons, complete with soothing Richard Dreyfuss narration.

Ponder for a minute the plight of one-hit wonders. Plucked from obscurity on the basis of a catchy demo or exhilarating live performance, they’re catapulted into the limelight just long enough to get spoiled by it. One moment they’re relative unknowns, then they’re suddenly being feted like deities before crashing back into semi-obscurity and wondering where in the hell everyone went and what they’re supposed to do with their post-hit existences. That’s got to fuck with your head. It’s entirely possible that Plain White T’s will release an endless stream of smash albums (no wait, it isn’t), but to me they seem like the quintessential one-hit wonders, an aggregation of sensitive white boys who captured the public’s imagination with “Hey There Delilah,” a painfully earnest acoustic ballad that sounds suspiciously like something a 14-year-old might write on his very first starter acoustic guitar in an attempt to win back his first girlfriend. It’s as messily, uncomfortably intimate as a teenager girl’s diary, but it’s also vulnerable and sweet in a way that makes it a shame it’s such a goddamn terrible song. It might have wowed co-eds at the student union, but on a slick compilation like this it feels homemade and even amateurish, which is both a major fault and its greatest strength.

When I first heard Nickelback’s “Rockstar” I thought it was a joke, which it kind of is. Surely no one could deliberately make such an agonizingly awful song. It had to be some sort of deadpan satire of bloated cock-rock, right? Sure, “Rockstar” is ostensibly a “funny” song, but its “satire” of rock-star decadence would have felt lame and depressingly familiar back in 1972. It sounds prehistoric now. Being blissfully unfamiliar with Nickelback, I assumed the group must have been performing a parody of testosterone-poisoned, over-the-top, grunting ’80s and ’90s cock-rock, with its infernal bleating and obnoxious over-production. Then I discovered that Nickelback sounds like that all the time. It’s a dumb song that thinks it’s smart, the work of a bunch of burnouts who suddenly think they’ve turned into Elvis Costello or Randy Newman. It is, in other words, not a very good song. In fact, it’s fucking awful, just the worst. My father taught me that hate is a strong word that should be reserved for subjects worthy of its intensity: the Nazis, sex criminals, Young Republicans. Well, I fucking hate “Rockstar.”

Just as Nickelback comes off as a groaning parody of a neanderthal rock act on “Rockstar,” newcomer J. Holiday almost plays like an over-the-top spoof of heavy-breathing quiet storm Casanovas on “Bed.” Holiday delivers a honey-coated hard sell in which he promises to fuck the object of his desire into a comatose state, only to begin the marathon fucking anew the moment she wakes up from her harrowing ordeal… I mean, ecstatic, hours-long fuckfest. To give Holiday credit, he does stop short of promising to fuck his girlfriend to death. He’s subtler than that, and as Kanye, Soulja Boy, Timbaland, Nickelback, and the other pop stars of Now 26 have shown us, great music is all about subtlety. Oh and deeply meaningful lyrics about important subjects.

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Up Next on THEN!: Fergie samples the theme song to a Frank Tashlin movie, Kanye gets lost in flashing lights, Alicia Keys hearts Swizz Beatz, and Taylor Swift has teardrops on her guitar, saccharine on the inside of her soul.

Outside the Bubble: What else was happening in pop music in winter 2007